1. Field of the Invention:
This invention relates to the synthesis of cis-1,4-cyclohexadiene dioxide, said compound being useful in the total synthesis of aminoglycosides.
2. Description of the Prior Art:
A. Tetsuo Suami et al, J. Org. Chem., 40, 547 (1975) describe the synthesis of four position isomers of dideoxystreptamine.
B. R. T. Testa et al, The Journal of Antibiotics 27, 917 (1974), describe the fermentation of aminoglycosides possessing a 2,5-dideoxystreptamine moiety when 2,5-dideoxystreptamine was added to the fermentation media as a precursor.
C. The kanamycins are known antibiotics described in Merck Index, 8th ed., pp. 597-598. Kanamycin A is a compound having the formula ##STR1##
D. T. W. Craig et al, J. Org. Chem., 32, 3743 (1967), reported that bis-epoxidation of 1,4-cyclohexadiene with perbenzoic acid or monoperphthalic acid produced exclusively the trans-epoxide, whereas bis-epoxidation with m-chloroperbenzoic acid or peracetic acid produced a 2:1 mixture of trans- and cis-epoxides respectively. They further reported the cis-epoxide could not be separated from the mixture due to its tendency to form a 1:1 crystalline complex with the trans-epoxide.